Chicago tried this decades ago with the State Street Mall project [1]. It turned out to be an overall flop, with stores seeing reduced traffic, and by 1993 it was gone and good riddance. As a pedestrian, I hated it when I worked downtown.
Maybe they'll do something on Market Street that will work better, or perhaps it might be a better fit there than in Chicago, but I wish them luck, because they're going to need it.
Nobody is on Market to get to a destination on Market. You can’t park for the vast majority of it, and there are literally no driveways. This change mostly eliminates through traffic that drags down bus service.
King St. in Toronto is a kind of hybrid project[0] where cars have local access, but must turn either right or left at a bunch of intersections. On-street parking is gone. It's been a resounding success specifically for local businesses, which is interesting (and not surprising to me, but opposite of what you say happened in Chicago). More comparable climate to Chicago too.
Probably more like 10 months. I imagine there's a shoulder season in the spring and fall where Chicago is more desirable, from a weather standpoint, than cool and windy SF, before it gets too hot and humid in Chicago's summer.
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There seems to be an alternative interpretation the State Steet project and its failure here: https://www.wbez.org/shows/dynamic-range/the-short-sad-life-... but you have to listen to the recording of a radio program for all the details, which I didn't do.
Anyway, I live in Vienna where we have had pedestrianized shopping streets since 1971. Before every single project there is a huge discussion that this will kill all commerce, and in these 49 years that has never happened -- quite on the contrary. These projects are so successful and popular that recently even the chamber of commerce, previously a huge opponent, called for more of them.
Is the US that different? Maybe. Or maybe it just needs its own learning process.
Maybe they'll do something on Market Street that will work better, or perhaps it might be a better fit there than in Chicago, but I wish them luck, because they're going to need it.
[1] https://www.chicagotribune.com/opinion/commentary/ct-opinion...